The growing trend of collecting data about individuals to track past actions and infer future attitudes and behaviors has fueled popular and scholarly interest in the erosion of privacy. Recent shifts in technologies around machine learning and artificial intelligence have intensified these concerns. This editorial introduces the articles in the special theme on digital resignation and privacy cynicism: concepts developed in the past decade to explain the growing powerlessness individuals feel in relation to their digital privacy even as they continue to experience consternation over the collection and use of their personal information. The papers in this special theme engage and extend existing research on these topics. The original articles and commentaries pose theoretical and practical questions related to the ways people confront the powerful institutional forces that increasingly shape many aspects of the information environment. They employ several methodologies and theoretical perspectives and extend the range of geographic, political, cultural, and institutional contexts in which privacy cynicism and digital resignation can be identified and examined. In addition to contextualizing these contributions, this editorial maps a range of related concepts including digital resignation, privacy cynicism, privacy apathy, surveillance realism, privacy fatigue, and privacy helplessness. It concludes by identifying key themes across the papers in this collection and provides directions for future research.